JPH0243749B2 - - Google Patents
Info
- Publication number
- JPH0243749B2 JPH0243749B2 JP56043044A JP4304481A JPH0243749B2 JP H0243749 B2 JPH0243749 B2 JP H0243749B2 JP 56043044 A JP56043044 A JP 56043044A JP 4304481 A JP4304481 A JP 4304481A JP H0243749 B2 JPH0243749 B2 JP H0243749B2
- Authority
- JP
- Japan
- Prior art keywords
- ascorbic acid
- present
- compound
- added
- dipivaloyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 19
- 229960005070 ascorbic acid Drugs 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 11
- 239000002211 L-ascorbic acid Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000011668 ascorbic acid Substances 0.000 description 9
- 235000010323 ascorbic acid Nutrition 0.000 description 9
- 239000003814 drug Substances 0.000 description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 229940079593 drug Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 210000000695 crystalline len Anatomy 0.000 description 4
- 239000003889 eye drop Substances 0.000 description 4
- 229940012356 eye drops Drugs 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- -1 Acetyl ascorbic acid Chemical compound 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 208000002177 Cataract Diseases 0.000 description 2
- 235000000069 L-ascorbic acid Nutrition 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- POXUQBFHDHCZAD-UHFFFAOYSA-N 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,4-dihydroxy-2h-furan-5-one Chemical compound O1C(C)(C)OCC1C1C(O)=C(O)C(=O)O1 POXUQBFHDHCZAD-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 101100379081 Emericella variicolor andC gene Proteins 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 150000000996 L-ascorbic acids Chemical class 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 210000001742 aqueous humor Anatomy 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 229940096978 oral tablet Drugs 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/62—Three oxygen atoms, e.g. ascorbic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/12—Ophthalmic agents for cataracts
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Ophthalmology & Optometry (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56043044A JPS57156479A (en) | 1981-03-24 | 1981-03-24 | Ascorbic acid derivative |
| IT20295/82A IT1150726B (it) | 1981-03-24 | 1982-03-19 | Derivati dell'acido ascorbico |
| PCT/JP1982/000076 WO1982003393A1 (en) | 1981-03-24 | 1982-03-19 | Ascorbic acid derivatives |
| GB08231472A GB2109382B (en) | 1981-03-24 | 1982-03-19 | Ascorbic acid derivatives |
| EP82900989A EP0074411B1 (en) | 1981-03-24 | 1982-03-19 | Ascorbic acid derivatives |
| DE3239721T DE3239721C2 (de) | 1981-03-24 | 1982-03-19 | Ascorbinsäure-Derivate, Verfahren zu ihrer Herstellung und therapeutisches Mittel |
| ES510694A ES8303393A1 (es) | 1981-03-24 | 1982-03-23 | Un procedimiento para preparar derivados del acido ascorbico. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56043044A JPS57156479A (en) | 1981-03-24 | 1981-03-24 | Ascorbic acid derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57156479A JPS57156479A (en) | 1982-09-27 |
| JPH0243749B2 true JPH0243749B2 (es) | 1990-10-01 |
Family
ID=12652892
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56043044A Granted JPS57156479A (en) | 1981-03-24 | 1981-03-24 | Ascorbic acid derivative |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0074411B1 (es) |
| JP (1) | JPS57156479A (es) |
| DE (1) | DE3239721C2 (es) |
| ES (1) | ES8303393A1 (es) |
| GB (1) | GB2109382B (es) |
| IT (1) | IT1150726B (es) |
| WO (1) | WO1982003393A1 (es) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4552895A (en) * | 1983-03-14 | 1985-11-12 | Eli Lilly And Company | Furo[3,2-b]furan-2-(3H)-ones |
| US4886795A (en) * | 1984-06-20 | 1989-12-12 | Schachar Ronald A | Treatment and prevention of retinal edema with dopaminergic antagonists |
| US4886815A (en) * | 1984-06-20 | 1989-12-12 | Schachar Ronald A | Treatment and prevention of retinal edema with dopaminergic antagonists |
| FR2580644B1 (fr) * | 1985-04-23 | 1990-01-12 | Kao Corp | Derives de l'acide ascorbique |
| ZA852614B (en) * | 1985-05-17 | 1986-10-09 | Takeda Chemical Industries, Ltd. | Ascorbic acid ethers and their production |
| JPH0813739B2 (ja) * | 1986-12-03 | 1996-02-14 | 武田薬品工業株式会社 | 白内障治療剤 |
| FR2715156B1 (fr) * | 1994-01-20 | 1996-03-01 | Oreal | Mono-esters d'acide cinnamique ou de ses dérivés et de vitamine C, leur procédé de préparation et leur utilisation comme anti-oxydants dans des compositions cosmétiques, pharmaceutiques ou alimentaires. |
| US9550744B2 (en) * | 2013-09-25 | 2017-01-24 | University Of Florida Research Foundation, Inc. | Vitamin C prodrugs and uses thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4987655A (es) * | 1972-12-27 | 1974-08-22 | ||
| US4208434A (en) * | 1978-07-11 | 1980-06-17 | The Coca-Cola Company | Color stable food containing anthocyanic pigments and bio-available vitamin C and process for its production |
-
1981
- 1981-03-24 JP JP56043044A patent/JPS57156479A/ja active Granted
-
1982
- 1982-03-19 GB GB08231472A patent/GB2109382B/en not_active Expired
- 1982-03-19 IT IT20295/82A patent/IT1150726B/it active
- 1982-03-19 DE DE3239721T patent/DE3239721C2/de not_active Expired
- 1982-03-19 WO PCT/JP1982/000076 patent/WO1982003393A1/ja active IP Right Grant
- 1982-03-19 EP EP82900989A patent/EP0074411B1/en not_active Expired
- 1982-03-23 ES ES510694A patent/ES8303393A1/es not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| J.AGRIC FOOD CHEM=1980 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0074411A4 (en) | 1983-07-04 |
| IT8220295A0 (it) | 1982-03-19 |
| IT1150726B (it) | 1986-12-17 |
| ES510694A0 (es) | 1983-02-01 |
| DE3239721C2 (de) | 1986-02-27 |
| WO1982003393A1 (en) | 1982-10-14 |
| ES8303393A1 (es) | 1983-02-01 |
| JPS57156479A (en) | 1982-09-27 |
| EP0074411A1 (en) | 1983-03-23 |
| EP0074411B1 (en) | 1986-05-28 |
| DE3239721T1 (de) | 1983-03-24 |
| GB2109382A (en) | 1983-06-02 |
| GB2109382B (en) | 1985-07-24 |
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